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Portland

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Portland Flights as Low as $215

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Breeze Airways
Fri, May 16 - Mon, May 26
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$215 Roundtrip, found 3 days ago
$215
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Fri, May 16 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, May 26, priced at $215 found 3 days ago
Breeze Airways
Fri, May 16 - Fri, May 23
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$234 Roundtrip, found 3 days ago
$234
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Fri, May 16 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Fri, May 23, priced at $234 found 3 days ago
Breeze Airways
Mon, May 19 - Fri, May 23
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$244 Roundtrip, found 3 days ago
$244
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Mon, May 19 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Fri, May 23, priced at $244 found 3 days ago
Breeze Airways
Fri, May 16 - Mon, May 19
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$247 Roundtrip, found 1 day ago
$247
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, May 16 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, May 19, priced at $247 found 1 day ago
Breeze Airways
Mon, May 19 - Fri, May 23
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$257 Roundtrip, found 1 day ago
$257
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Mon, May 19 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Fri, May 23, priced at $257 found 1 day ago
Avelo Airlines
Fri, May 16 - Sun, May 18
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$279 Roundtrip, found 3 days ago
$279
Roundtrip
found 3 days ago
Select Avelo Airlines flight, departing Fri, May 16 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Sun, May 18, priced at $279 found 3 days ago
Breeze Airways
Fri, May 16 - Sun, May 18
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$346 Roundtrip, found 1 day ago
$346
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, May 16 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Sun, May 18, priced at $346 found 1 day ago
Breeze Airways
Fri, May 16 - Sat, May 17
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$347 Roundtrip, found 1 day ago
$347
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, May 16 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Sat, May 17, priced at $347 found 1 day ago
Breeze Airways
Mon, May 19 - Wed, May 21
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$356 Roundtrip, found 1 day ago
$356
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Mon, May 19 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Wed, May 21, priced at $356 found 1 day ago
Breeze Airways
Fri, May 16 - Thu, May 22
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$365 Roundtrip, found 1 day ago
$365
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, May 16 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Thu, May 22, priced at $365 found 1 day ago
Breeze Airways
Fri, May 16 - Sun, May 25
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$372 Roundtrip, found 1 day ago
$372
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, May 16 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Sun, May 25, priced at $372 found 1 day ago
Breeze Airways
Mon, May 19 - Thu, May 22
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$375 Roundtrip, found 1 day ago
$375
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Mon, May 19 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Thu, May 22, priced at $375 found 1 day ago
Breeze Airways
Sun, May 18 - Mon, May 26
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$380 Roundtrip, found 3 days ago
$380
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sun, May 18 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, May 26, priced at $380 found 3 days ago
Breeze Airways
Mon, May 19 - Sun, May 25
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$381 Roundtrip, found 1 day ago
$381
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Mon, May 19 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Sun, May 25, priced at $381 found 1 day ago
Breeze Airways
Sun, May 18 - Fri, May 23
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$399 Roundtrip, found 3 days ago
$399
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sun, May 18 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Fri, May 23, priced at $399 found 3 days ago
Breeze Airways
Sun, May 18 - Fri, May 23
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$412 Roundtrip, found 1 day ago
$412
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sun, May 18 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Fri, May 23, priced at $412 found 1 day ago

Cheap Flights to Portland

Fall in love at first flight with your vacation to Portland by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Portland on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Portland, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Portland

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Portland with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the HFD airport.

What is the cheapest month to fly to Portland?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Portland are in May, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Portland?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Portland.

What airport is best to fly into Portland?

When you’re planning your trip to Portland, convenience is the name of the game. Luckily, Portland Tweed - New Haven Regional Airport is nearby so you can deplane and get going on checking off everything on your Portland must-do list.

How much are flights to Portland?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Portland on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $215, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Portland?

The trick to saving a stack of cash on your flight to Portland? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $215 right now, why wait?

Portland Flight Information
Destination airport
Tweed - New Haven Regional
Destination airport IATA code
HVN
Roundtrip price
$215

Last Minute Hotel Deals in Portland

Solano Inn
Solano Inn
2.5 out of 5
1503 Portland-Cobalt Rd, Portland, CT
The price is $118 per night from May 5 to May 6
$118
includes taxes & fees
May 5 - May 6
Stay at this hotel in Portland. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Arrigoni Winery and Harbor Park are located ...
9/10 Wonderful! (122 reviews)
"Staff was excellent. Super friendly and welcoming.👏👏"

Reviewed on Apr 28, 2025

Solano Inn
Clarion Inn
Clarion Inn
3 out of 5
201 Washington Avenue, North Haven, CT
The price is $108 per night from May 7 to May 8
$108
includes taxes & fees
May 7 - May 8
Book a stay at this business-friendly hotel in North Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
7.4/10 Good! (1,007 reviews)
"Excellent customer service"

Reviewed on Apr 22, 2025

Clarion Inn
Holiday Inn Express Southington by IHG
Holiday Inn Express Southington by IHG
2.5 out of 5
120 Laning St, Southington, CT
The price is $117 per night from May 4 to May 5
$117
includes taxes & fees
May 4 - May 5
Book a stay at this business-friendly hotel in Southington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.6/10 Excellent! (1,001 reviews)
One Night Turned Into Four
"I stayed at this location with my son the night before a conference in downtown Hartford. The hotel was well kept and staff were welcoming. We had anticipated on staying at another hotel downtown for the rest of our stay but unfortunately did not feel safe in that neighborhood. We immediately returned ..."

Reviewed on Apr 29, 2025

Holiday Inn Express Southington by IHG
The Goodwin Hotel
The Goodwin Hotel
3.5 out of 5
1 Haynes St, Hartford, CT
The price is $212 per night from May 22 to May 23
$212
includes taxes & fees
May 22 - May 23
Stay at this 3.5-star hotel in Hartford. Enjoy free WiFi, a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff and the clean ...
9/10 Wonderful! (1,001 reviews)
"The room Was really hot. But it was nice and clean and swanky"

Reviewed on May 1, 2025

The Goodwin Hotel
Motel 6 Wethersfield, CT - Hartford
Motel 6 Wethersfield, CT - Hartford
2 out of 5
1341 Silas Deane Hwy, Wethersfield, CT
The price is $75 per night from May 5 to May 6
$75
includes taxes & fees
May 5 - May 6
Stay at this motel in Wethersfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
6.4/10 (1,001 reviews)
"Security"

Reviewed on Apr 28, 2025

Motel 6 Wethersfield, CT - Hartford
Woodspring Suites Newington - Hartford South
Woodspring Suites Newington - Hartford South
2.5 out of 5
712 Cedar Street, Newington, CT
The price is $115 per night from May 4 to May 5
$115
includes taxes & fees
May 4 - May 5
Stay at this hotel in Newington. Enjoy free WiFi and free parking. Popular attractions Iwo Jima Survivors Memorial Park and Westfarms Mall are located ...
7.6/10 Good! (79 reviews)
"Residents are rude but hotel is okay."

Reviewed on Apr 28, 2025

Woodspring Suites Newington - Hartford South
Best Western Hartford Hotel & Suites
Best Western Hartford Hotel & Suites
2.5 out of 5
185 Brainard Rd, Hartford, CT
The price is $111 per night from May 8 to May 9
$111
includes taxes & fees
May 8 - May 9
Stay at this hotel in Hartford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
7.6/10 Good! (999 reviews)
"Staff was friendly and helpful. Room was clean, looked newly painted, remodeled. Refrigerator and microwave worked and were clean. Beds were very comfortable and room was very quiet. Elevator was quick. 24 hour coffee was good. Breakfast was okay. Zero complaints. Would stay again."

Reviewed on Apr 28, 2025

Best Western Hartford Hotel & Suites
Avon Old Farms Hotel
Avon Old Farms Hotel
3.5 out of 5
279 Avon Mountain Rd, Avon, CT
The price is $216 per night from May 4 to May 5
$216
includes taxes & fees
May 4 - May 5
Stay at this hotel in Avon. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
8.2/10 Very Good! (1,002 reviews)
"I liked everything about this hotel, except the restaurant. Very limited menu and the food was less than average. Pretty sure the Alfredo sauce was from a jar. If you stay here, plan to eat at The North House right across the street. Excellent menu and outstanding food."

Reviewed on Apr 27, 2025

Avon Old Farms Hotel
See all 658 properties in Portland
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.